RU2439069C2 - Способ получения 1,3-оксатиолановых нуклеозидов - Google Patents

Способ получения 1,3-оксатиолановых нуклеозидов Download PDF

Info

Publication number
RU2439069C2
RU2439069C2 RU2004125183/04A RU2004125183A RU2439069C2 RU 2439069 C2 RU2439069 C2 RU 2439069C2 RU 2004125183/04 A RU2004125183/04 A RU 2004125183/04A RU 2004125183 A RU2004125183 A RU 2004125183A RU 2439069 C2 RU2439069 C2 RU 2439069C2
Authority
RU
Russia
Prior art keywords
mixture
reaction
oxathiolane
pyrimidine
mmol
Prior art date
Application number
RU2004125183/04A
Other languages
English (en)
Russian (ru)
Other versions
RU2004125183A (ru
Inventor
Джордж Р. ПЭЙНТЕР (US)
Джордж Р. ПЭЙНТЕР
Деннис К. ЛИОТТА (US)
Деннис К. Лиотта
Меррик ЭЛМОНД (US)
Меррик ЭЛМОНД
Дэррил КЛИРИ (US)
Дэррил КЛИРИ
Хосе СОРИЯ (US)
Хосе СОРИЯ
Маркос Луис ШНАЙДМАН (US)
Маркос Луис ШНАЙДМАН
Original Assignee
Гайлид Сайенсиз, Инк.
Эмори Юниверсити
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Гайлид Сайенсиз, Инк., Эмори Юниверсити filed Critical Гайлид Сайенсиз, Инк.
Publication of RU2004125183A publication Critical patent/RU2004125183A/ru
Application granted granted Critical
Publication of RU2439069C2 publication Critical patent/RU2439069C2/ru

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D473/00Heterocyclic compounds containing purine ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • A61P31/18Antivirals for RNA viruses for HIV
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D327/00Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04Five-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D411/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/02Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D411/04Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Virology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Communicable Diseases (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
RU2004125183/04A 1998-08-12 1999-08-12 Способ получения 1,3-оксатиолановых нуклеозидов RU2439069C2 (ru)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US9621498P 1998-08-12 1998-08-12
US60/096,214 1998-08-12
US12284199P 1999-03-04 1999-03-04
US60/122,841 1999-03-04

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
RU2001106606/04A Division RU2244712C2 (ru) 1998-08-12 1999-08-12 Способ получения 1,3-оксатиоланового нуклеозида, способ получения производного 1,3-оксатиоланил-5-она

Publications (2)

Publication Number Publication Date
RU2004125183A RU2004125183A (ru) 2006-01-27
RU2439069C2 true RU2439069C2 (ru) 2012-01-10

Family

ID=26791450

Family Applications (2)

Application Number Title Priority Date Filing Date
RU2004125183/04A RU2439069C2 (ru) 1998-08-12 1999-08-12 Способ получения 1,3-оксатиолановых нуклеозидов
RU2001106606/04A RU2244712C2 (ru) 1998-08-12 1999-08-12 Способ получения 1,3-оксатиоланового нуклеозида, способ получения производного 1,3-оксатиоланил-5-она

Family Applications After (1)

Application Number Title Priority Date Filing Date
RU2001106606/04A RU2244712C2 (ru) 1998-08-12 1999-08-12 Способ получения 1,3-оксатиоланового нуклеозида, способ получения производного 1,3-оксатиоланил-5-она

Country Status (17)

Country Link
US (4) US6215004B1 (ja)
EP (4) EP1361223B1 (ja)
JP (4) JP4249393B2 (ja)
KR (3) KR100856416B1 (ja)
CN (1) CN1141305C (ja)
AT (2) ATE292631T1 (ja)
AU (2) AU771779B2 (ja)
BR (1) BR9912951B1 (ja)
CA (3) CA2714085C (ja)
DE (2) DE69921829T2 (ja)
ES (2) ES2232169T3 (ja)
HK (2) HK1038921A1 (ja)
IL (4) IL141359A0 (ja)
MX (1) MXPA01001552A (ja)
PT (2) PT1104415E (ja)
RU (2) RU2439069C2 (ja)
WO (1) WO2000009494A1 (ja)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5684164A (en) * 1988-04-11 1997-11-04 Biochem Pharma Inc. Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
KR100856416B1 (ko) * 1998-08-12 2008-09-04 길리애드 사이언시즈, 인코포레이티드 1,3-옥사티올란 뉴클레오시드의 제조 방법
CA2308559C (en) 2000-05-16 2005-07-26 Brantford Chemicals Inc. 1,3-oxathiolan-5-ones useful in the production of antiviral nucleoside analogues
AU2008202336B2 (en) * 2001-03-01 2011-11-10 Abbvie Inc. Polymorphic and other crystalline forms of cis-FTC
KR101015510B1 (ko) * 2001-03-01 2011-02-16 길리애드 사이언시즈, 인코포레이티드 시스-ftc의 다형 및 기타 결정형
BRPI0210444B1 (pt) * 2001-06-15 2017-06-20 Shire Canada Inc. Stereo-relevant process for the preparation of nucleosidal analogs
CA2351049C (en) 2001-06-18 2007-03-13 Brantford Chemicals Inc. Process for recovery of the desired cis-1,3-oxathiolane nucleosides from their undesired trans-isomers
WO2003051298A2 (en) * 2001-12-14 2003-06-26 Pharmasset Ltd. Preparation of intermediates useful in the synthesis of antiviral nucleosides
WO2004009583A2 (en) * 2002-07-19 2004-01-29 Garst Michael E Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor
ES2360096T3 (es) 2002-08-06 2011-05-31 Pharmasset, Inc. Procedimientos de preparación de nucleosidos de 1,3-dioxolano.
AU2004206821C1 (en) 2003-01-14 2009-10-01 Gilead Sciences, Inc. Compositions and methods for combination antiviral therapy
WO2005056870A1 (ja) * 2003-12-09 2005-06-23 Asahi Glass Company, Limited 可視光で光触媒活性を有するTi酸化物膜およびその製造方法
US7785839B2 (en) 2004-02-03 2010-08-31 Emory University Methods to manufacture 1,3-dioxolane nucleosides
EP2086955A2 (en) * 2006-10-30 2009-08-12 Lupin Ltd. An improved process for the manufacture of cis(-)-lamivudine
CN101842370B (zh) * 2007-09-28 2014-02-19 阿维克沙有限公司 手性拆分2-取代的4-取代的1,3-氧硫杂环戊烷的方法
EP2048151A1 (en) * 2007-10-10 2009-04-15 Cilag AG Method for producing nucleosides by direct glycosylation of the nucleoside base
EP2050757A1 (en) * 2007-10-10 2009-04-22 Cilag AG Method of producing 2' -deoxy-5-azacytidine (Decitabine)
WO2010055526A1 (en) * 2008-11-12 2010-05-20 Lupin Limited A novel polymorph of emtricitabine and a process for preparing of the same
US20110282046A1 (en) 2009-01-19 2011-11-17 Rama Shankar Process for preparation of cis-nucleoside derivative
EP2454244B1 (en) 2009-07-15 2013-06-26 Lupin Limited An improved process for preparation of efavirenz
WO2011141805A2 (en) 2010-05-14 2011-11-17 Lupin Limited An improved process for the manufacture of lamivudine
WO2013021290A1 (en) 2011-08-05 2013-02-14 Lupin Limited A stereoselective process for preparation of 1,3-oxathiolane nucleosides
CN106478618A (zh) * 2016-10-14 2017-03-08 上海礼泰医药科技有限公司 恩曲他滨氢卤酸盐的制备方法
CN109553610B (zh) * 2018-12-21 2020-10-27 江西富祥药业股份有限公司 一种恩曲他滨异构体的制备方法
CN115043823A (zh) * 2022-06-28 2022-09-13 江苏普信制药有限公司 一种恩曲他滨的合成方法

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5466806A (en) 1989-02-08 1995-11-14 Biochem Pharma Inc. Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
NZ228645A (en) 1988-04-11 1991-09-25 Iaf Biochem Int 1,3-dioxolane derivatives substituted in the 5th position by a purine or pyrimidine radical; treatment of viral infections
US5041449A (en) 1988-04-11 1991-08-20 Iaf Biochem International, Inc. 4-(nucleoside base)-substituted-1,3-dioxolanes useful for treatment of retroviral infections
US5047407A (en) 1989-02-08 1991-09-10 Iaf Biochem International, Inc. 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
US5684164A (en) 1988-04-11 1997-11-04 Biochem Pharma Inc. Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
US5204466A (en) * 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds
US5276151A (en) 1990-02-01 1994-01-04 Emory University Method of synthesis of 1,3-dioxolane nucleosides
US5700937A (en) 1990-02-01 1997-12-23 Emory University Method for the synthesis, compositions and use of 2'-deoxy-5-fluoro-3'-thiacytidine and related compounds
US6642245B1 (en) 1990-02-01 2003-11-04 Emory University Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane
US6069252A (en) 1990-02-01 2000-05-30 Emory University Method of resolution and antiviral activity of 1,3-oxathiolane nucleoside enantiomers
GB9009861D0 (en) * 1990-05-02 1990-06-27 Glaxo Group Ltd Chemical compounds
US5587480A (en) 1990-11-13 1996-12-24 Biochem Pharma, Inc. Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties
WO1992010496A1 (en) * 1990-12-05 1992-06-25 University Of Georgia Research Foundation, Inc. ENANTIOMERICALLY PURE β-L-(-)-1,3-OXATHIOLANE NUCLEOSIDES
US5248776A (en) 1990-12-05 1993-09-28 University Of Georgia Research Foundation, Inc. Process for enantiomerically pure β-L-1,3-oxathiolane nucleosides
US5444063A (en) 1990-12-05 1995-08-22 Emory University Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity
IL100965A (en) * 1991-02-22 1999-12-31 Univ Emory 2 - Hydroxymethyl - 5 -) 5 - Fluorocytocin - 1 - Eyal (- 1, 3 - Oxathiolane, its resolution and pharmaceuticals containing it
GB9104740D0 (en) 1991-03-06 1991-04-17 Wellcome Found Antiviral nucleoside combination
KR100270806B1 (ko) 1991-03-06 2000-11-01 템블 존 엘 5-플루오로-2`-데옥시-3`-티아시티딘을 함유하는 b형 간염 치료를 위한 약제
IT1244501B (it) 1991-03-22 1994-07-15 Sigma Tau Ind Farmaceuti Derivati amminoacilici e oligopeptidici dell'allopurinolo dotati di attivita' immunostimolante e composizioni farmaceutiche che li contengono
WO1992018517A1 (en) 1991-04-17 1992-10-29 Yale University Method of treating or preventing hepatitis b virus
GB9110874D0 (en) 1991-05-20 1991-07-10 Iaf Biochem Int Medicaments
ZA923640B (en) 1991-05-21 1993-02-24 Iaf Biochem Int Processes for the diastereoselective synthesis of nucleosides
GB9116601D0 (en) 1991-08-01 1991-09-18 Iaf Biochem Int 1,3-oxathiolane nucleoside analogues
GB9311709D0 (en) 1993-06-07 1993-07-21 Iaf Biochem Int Stereoselective synthesis of nucleoside analogues using bicycle intermediate
IL113432A (en) * 1994-04-23 2000-11-21 Glaxo Group Ltd Process for the diastereoselective synthesis of nucleoside analogues
WO1996001873A1 (fr) 1994-07-08 1996-01-25 Mitsui Petrochemical Industries, Ltd. Composition de resine polyester thermoplastique
GB9506644D0 (en) 1995-03-31 1995-05-24 Wellcome Found Preparation of nucleoside analogues
GB9525606D0 (en) * 1995-12-14 1996-02-14 Iaf Biochem Int Method and compositions for the synthesis of dioxolane nucleosides with › - configuration
TW318283B (en) 1996-12-09 1997-10-21 United Microelectronics Corp Multi-level read only memory structure and manufacturing method thereof
KR100856416B1 (ko) * 1998-08-12 2008-09-04 길리애드 사이언시즈, 인코포레이티드 1,3-옥사티올란 뉴클레오시드의 제조 방법
US9308044B2 (en) 2002-04-08 2016-04-12 Medtronic Ardian Luxembourg S.A.R.L. Methods for therapeutic renal neuromodulation
US9109124B2 (en) 2011-06-01 2015-08-18 Xerox Corporation Solid ink compositions comprising semicrystalline oligomer resins
JP5800924B2 (ja) 2014-01-20 2015-10-28 ファナック株式会社 回転工具の回転振れ及び動バランス調整機構

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Woo-Baeg Choi et al. In Situ Complexation Directs the Stereochemistry of N-Glycosylation in the Synthesis of Oxathiolanyl and Dioxolanyl Nucleoside Analogues. // J. Am. Chem. Soc. 1991. 113, 9377-9379. *

Also Published As

Publication number Publication date
EP1361223A1 (en) 2003-11-12
JP5203897B2 (ja) 2013-06-05
IL173745A (en) 2010-05-31
JP2002522534A (ja) 2002-07-23
DE69924651D1 (de) 2005-05-12
DE69921829D1 (de) 2004-12-16
EP1104415A1 (en) 2001-06-06
KR100687194B1 (ko) 2007-02-27
HK1156604A1 (en) 2012-06-15
AU2004202930B2 (en) 2008-05-08
US20030144532A1 (en) 2003-07-31
PT1104415E (pt) 2005-03-31
JP4249393B2 (ja) 2009-04-02
JP2014132026A (ja) 2014-07-17
IL201293A0 (en) 2010-05-31
EP1104415B1 (en) 2004-11-10
EP2322518A1 (en) 2011-05-18
IL141359A0 (en) 2002-03-10
KR20060063991A (ko) 2006-06-12
EP2322518B1 (en) 2015-02-25
PT2322518E (pt) 2015-06-08
KR101208429B1 (ko) 2012-12-05
JP5547772B2 (ja) 2014-07-16
WO2000009494A1 (en) 2000-02-24
RU2004125183A (ru) 2006-01-27
KR100856416B1 (ko) 2008-09-04
ATE282034T1 (de) 2004-11-15
AU5675299A (en) 2000-03-06
IL141359A (en) 2006-07-05
US6518425B1 (en) 2003-02-11
BR9912951B1 (pt) 2012-01-10
US6939965B2 (en) 2005-09-06
CN1313858A (zh) 2001-09-19
CA2340214C (en) 2007-10-30
KR20010072428A (ko) 2001-07-31
KR20070094667A (ko) 2007-09-20
BR9912951A (pt) 2001-10-02
ATE292631T1 (de) 2005-04-15
ES2232169T3 (es) 2005-05-16
JP2009108080A (ja) 2009-05-21
US6576776B1 (en) 2003-06-10
MXPA01001552A (es) 2004-08-23
JP2012176974A (ja) 2012-09-13
ES2537540T3 (es) 2015-06-09
EP1535921A1 (en) 2005-06-01
IL173745A0 (en) 2006-07-05
CA2714085C (en) 2013-02-05
CA2714085A1 (en) 2000-02-24
JP5956492B2 (ja) 2016-07-27
RU2244712C2 (ru) 2005-01-20
AU771779B2 (en) 2004-04-01
HK1038921A1 (en) 2002-04-04
IL201293A (en) 2011-02-28
CA2340214A1 (en) 2000-02-24
AU2004202930A1 (en) 2004-07-29
CN1141305C (zh) 2004-03-10
EP1361223B1 (en) 2005-04-06
CA2563022A1 (en) 2000-02-24
DE69921829T2 (de) 2005-10-27
CA2563022C (en) 2010-11-23
AU2004202930C1 (en) 2008-11-13
US6215004B1 (en) 2001-04-10

Similar Documents

Publication Publication Date Title
RU2439069C2 (ru) Способ получения 1,3-оксатиолановых нуклеозидов
US5248776A (en) Process for enantiomerically pure β-L-1,3-oxathiolane nucleosides
WO1992010496A1 (en) ENANTIOMERICALLY PURE β-L-(-)-1,3-OXATHIOLANE NUCLEOSIDES
AU2008201983B2 (en) Method of manufacture of 1,3-oxathiolane nucleosides
MXPA06008722A (en) Methods to manufacture 1,3-dioxolane nucleosides

Legal Events

Date Code Title Description
FA92 Acknowledgement of application withdrawn (lack of supplementary materials submitted)

Effective date: 20100521

FZ9A Application not withdrawn (correction of the notice of withdrawal)

Effective date: 20110428